2-Chloroanisole → 2-Methoxyphenylacetone

Beteiligte Stoffe

Reaktionsschritte

This reaction is carried out in the same manner as the reaction in example 3. The difference is that, the reactants are o-methoxyphenyl chloride (142.3 mg, 1.0 mmol), palladium cinnamyl chloride (7.9 mg, 0.015 mmol), 2-Methoxy-6-(N-methyl-N-phenyl-amino) henyldicyclohexyl)phosphine (24.5 mg, 0.060 mmol), CS2CO3 (653.0 mg, 2.0 mmol) in 4.0 mL acetone at 90° C. for 16 h. 1-(2′-Methoxyphenyl)-2-propanone (147.7 mg) was obtained with a yield of 89% as liquid. 1H NMR (300 MHz, CDCl3) δ 7.29-7.22 (m, 1H, ArH), 7.14-7.09 (m, 1H, ArH), 6.94-6.84 (m, 2H, ArH), 3.79 (s, 3H, OCH3), 3.66 (s, 2H, CH2), 2.12 (s, 3H, COCH3); 13C NMR (75 MHz, CDCl3) δ 206.9, 157.2, 131.0, 128.4, 123.5, 120.5, 110.3, 55.2, 45.4, 29.1; IR (neat) v (cm−1) 3003, 2941, 2905, 2837, 1713, 1602, 1589, 1496, 1464, 1439, 1356, 1322, 1290, 1247, 1176, 1160, 1115, 1050, 1030; MS (70 eV, EI) m/z (%): 165 (M++1, 6.45), 164 (M+, 50.19), 91 (100).

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